US 2176516 A
Description (OCR text may contain errors)
' layers particularly used as a filter absorbing dis- Patented 11, 1939;
' UNI ED STATES PATIENT: aOFFlC-E,
rom uzmo Lana Guatav wilmanns, W
Wilhelm Schneider, Dela, Anhal assignora. by meane tuto Alla Ansco CorporatiomBlnghamton, N. Y., a corporation of Delaware so 1mm. Application a... 21, 1937. Serial No.-143,934. In Germany June 12, 1936,
5 mm. (CL- m Our present invention relates to polarizing turbing reflections in the photographic exposure.
One/of its objects is to provide an improved polarizing layercontaining metal salt, bromine or iodine addition products of 5- or 6-membered heterocyclic nitrogen bases. Further objects will be seen from the detailed specification following These substances surpass Herapathite in respect of double refraction, facility of crytallization and solubility. l
It has also been observed that not only iodine, but also bromine and metal salts, particularly heavy metal salts, for instance salts of copper and iron, may be added to these bases and that the bodies produced by this addition also exhibit double refraction.
The quaternary ammonium' salts of the 'afore- 'said products, for instance alkyl halides, and
-- alkyl sulfates, have particularly favorable propa erties, since they far exceed in stability the ordinary salts of the addition compounds. It fol lows that inthe use'of quaternary ammonium compound as compared with the known materiala twofold eifect, namely greater activity and improved durability,.is obtained and with it a con:
' siderable technical progress. t1The following examples illustrate the invenon: r v (1) 0.55 gram of 2.5-diphenyl oxa'z'ole ofthe formula a I N oar-11cm. I f i o v isdissolvedin 5cc.ofglacialaoeticacid andto thesolutionisaddedoneof' Iodine-n. 0.65 inConcentraluni hydrochloric acid..'...'.. .'..ec'.'- 2 Glacial acetic acid ..oc;; 10. I A crystalline precipitate is immediately produced v and the mixture is heated until this is dissolved. whereupomafter cooling. greenish glittering needles separate.
(2) 0.55 gram of 2.5-diphenyl oxazole is dissolved in 5 cc. of glacial acetic acid and to the solution thereis added a solution'oi Ferric chloride gram 0.25 Concentrated hydrochloric .acid.. cc 2 in Glacial acetic acid "cc..- 5
Brown crystals are immediately precipitated; these are dissolved by heating and on cooling the solution yellow brown needles of melting point to C. are obtained.
(3) 1.1 grams of 2.5-diphenyl oxa'zole are dissolved in 10 cc. of glacial acetic acid and to the solution there is added a hot solution of Cupric chloride (anhydrous) "gram". 0.7
Concentrated hydrochloric acid i oc 1 Glacial acetic acid cc 20 There separates immediately a brick red crystalline substance.
(4) 0.9 gram of 2.5-diphenyl oxaaole methyl iodide of the formula coujja v is dissolved in 30 cc. of glacial acetic acid and after cooling 6.25 cc. of an N-solution of bromine in glacial acetic acid are added. An orange I body. is immediately precipitated which after recrystallization from glacial acetic acid melts at (5) 3 grams of 2-methyi-benzothiazole ethyl iodide of theformula are'disaolvedinailcaofwaterahdtotheaolution are added 20 cc. of an N-aolution of iodine in potassium iodide. A black substance is immediately precipitated which crystallizes from alcohol in beautiful crystalshaving a green color. (6)1111. manner similarto that deecribedin Example 5 there are obtained from 3.5 gram! of '1 2-methyl-benaosele'nazole ethyliodide of. the formula v v v g H (7) In a similar manner to; that described in A 2. A polarizingbody comprising a set suspend- Example there is obtained frompi'coline ethyl iodide of the formula 1 mm a black oil which crystallizes after some time.
(8) In a similar manner to that described in Example 5 there is obtained from quinaldine ethyl iodide of the formula N CHI 1 C:Ht
and a solution of iodide in potassium iodide an oil which becomes crystalline after a short time.
The embedding of the substance ina layer and the orientation of the crystals follow the known methods.
A method of preparing polarizing layers is for instance disclosed in the above mentioned U. S. Patent 1,951,664.
What we. claim is:
1. A polarizing body comprising a set suspending medium and a mass of particles which are addition compounds constituted of a heterocylic nitrogen compound containing in its molecule only one heterocyclic nitrogen nucleus, said nu cleus being a member selected from the group consisting of a heterocyclic nitrogen nucleus having five ring members and a heterocylic nitrogen nucleus having six ring members, and of a comp'onent selected from the group consisting of metal salts, bromine and iodine, said particles being dispersed tan-immovably embedded in said suspending medium with their polg axes oriented in substantial parallelism.
ing medium and a mass of particles which are addition compounds constituted of a quaternary ammonium salt of a heterocylic nitrogen compound containing in its molecule only one hetero-' cyclic nitrogen nucleus, said nucleus being a member selected from the. group-consisting of a heterocylic nitrogen nucleus having five ring members and a heterocyclic nitrogen nucleus having six ring members, and of a compound se- .lected Irom the group consisting of metal salts,
bromine and iodine, said particles being dispersed and immovably embedded in said suspending medium with their polarizing axes oriented in substantial parallelism. I 3. A polarizing body comprising a set suspending medium and a mass of particles which are addition compounds constituted of 2.5-diphenyl oxazole methyl iodide and of bromine, said paraddition compounds constituted of 2-methyl-' benzothiazole ethyl iodide and oi iodine, said particles being dispersed and immovably embedded in said suspending medium with their v polarizing axes oriented in substantial parallelism.
5. A polarizing body comprising a set suspending medium and a mass of particles which are addition compounds constituted of 2-methylbenzoselenazole ethyl iodide and of iodine, said particles being dispersed and immovably embedded in said suspending medium withtheir polarizing axes oriented in substantial parallel-